Richard Haines is somewhat of a fashion-week anomaly—he’s a 61-year-old illustrator with a blog. In a past life, he was a womenswear designer for some of America’s biggest brands, such as Calvin Klein, Bill Blass, Perry Ellis, and Puff Daddy, but he threw all that in to focus on art in the digital age. He quickly gained traction, getting hired by everyone from J.Crew to The New York Times for his ability to make guys look far cooler on paper than they do in real life (you can only imagine what he does for models at runway shows). And recently, he received the ultimate validation: a gig illustrating Prada’s menswear collections, the fruits of which were released in book and T-shirt form. Haines gave us a sneak peek at his Spring ’14 illustrations from Prada (below, left), Jil Sander (below, right), and Andrea Incontri (bottom), which debut exclusively here. And below, the talent talks about flying on private jets with Calvin Klein, life as a blogger, and that one time three days ago when Beppe Modenese mistook him for Bill Cunningham.

—Isaac Hindin-Miller

When did you first come to the shows and what’s changed since then? Eighteen thirty-four [laughs]. I went to Paris fashion week in the early eighties, when I was designing, and a friend of mine, who was the editor of New York magazine, would take me to shows like Claude Montana and Thierry Mugler. It was this amazing moment in Paris. Back then I saw womenswear, now I see menswear, so the scale of the audience is different. The biggest thing [then] was this trend of sending out, like, eight models in the same outfit all at once. It was very dramatic, and that doesn’t seem to happen now. If anything, it’s gotten more intimate and more manageable. But the media has made fashion week very different, which is fascinating.

I’ve heard you say that people were dropping a lot more money back in those days. Yeah, it was a different time. It was easier to be in the fashion business, because there weren’t these constant collections to do. The stakes weren’t as high, and people did it with a lot more money. Now, there are more brands competing for less money. A couple of years after I started going to the collections in Paris, I was working at Calvin Klein, and it was a privately owned company—it was his company—so if he wanted to charter a jet, he would. We’d go to London and then the fabric shows in Milan, and then we’d go to Lake Como and stay at the Villa d’Este. It wasn’t bad.

What’s it like being one of the only illustrators at the shows? I love doing it. There’s something really exciting about sitting down and watching someone present and being able to draw it. I don’t think about whether I’m one of the only people doing this. I just love doing it, and it makes me happy. I just keep going.

What are your fashion-week essentials? I inevitably always forget one thing. I have little cases where I carry charcoal pencils, Moleskine notebooks—which reminds me, I need to buy a new one today—a charger for my cell phone, antidepressants…. And that’s it. When I first started doing this, I would forget paper, and I started drawing on envelopes and show notes and people loved that, so sometimes it works to my advantage.

What’s it like being a blogger of a certain age? Next question. Well, I have a special keyboard and each letter is the size of an iPhone. Anything else you’d like to know? People are surprised—you’re not the only person who’s mentioned that. Beppe Modenese came up to me on the first day in Milan and said, “Mr. Cunningham, Bill Cunningham?” so that was kind of disconcerting. But when I started my blog after working for all these huge companies, it was such an amazing feeling to just put something out there on my own without it being edited by a corporate company. I’m certainly not starting out, but I have the enthusiasm of someone who’s a lot younger, who feels psyched by media. I also have a really short attention span, and I think that that works to my favor, as opposed to the first fifty years of my life, when it didn’t work to my favor.

What are you most excited about here in Milan? Meeting a husband. This is the first time that I’ve gone to a group of shows. I was here last year for Prada, which was really thrilling. Now, I’m seeing more shows and getting a bigger picture. For me, the audience is fascinating.

Do you prefer drawing the shows or the audience members? Both. There’s always something to look at. If a show’s not as good as it should be, there’s still someone amazing sitting somewhere—some great shape. I mean, I can find something riveting on a subway car.

Are there any newcomers that you have your eye on? I’m looking forward to Carven and AMI in Paris. I think they’re amazing brands and they’re bringing something new to the table.

Everybody complains about Milan as a city, but what’s the silver lining for you? The silver lining is just to be here, the opportunity to be in this amazing place, in this rarefied world, where I see fashion shows all day and eat wonderful food and meet gorgeous people. Sometimes I have to stop myself and say, “This is your life.”

Is this a glamorous week for you? I think it looks glamorous to civilians, but it’s a lot of hard work. It’s a lot of stress. I want to produce wonderful drawings in the same way a photographer wants to make great pictures and editors want to do great work. Everybody wants to be at their best. It’s glamorous, but it’s hard glamour.